Sodium Bicarbonate → 4-chloro-2-(1-(6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715214Notes

Reaction equation

HRID 715214 reaction equation
Br[CH2:2][C:3]1[C:12]([Cl:13])=[N:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.Cl.[F:15][C:16]([F:31])([CH:28]([F:30])[F:29])[CH2:17][O:18][C:19]1[N:24]=[CH:23][C:22]([CH:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>>[Cl:13][C:12]1[C:3]2[CH2:2][N:27]([CH:25]([C:22]3[CH:23]=[N:24][C:19]([O:18][CH2:17][C:16]([F:31])([F:15])[CH:28]([F:30])[F:29])=[CH:20][CH:21]=3)[CH3:26])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylateHCID 874266151-(6-(2,2,3,3-Tetrafluoropropoxy)pyridin-3-yl)ethanamine hydrochloride

Product 1

HCID 898749994-chloro-2-(1-(6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 60%

Procedure

The title compound is prepared in 60% yield (137 mg, pale yellow oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (175 mg, 0.53 mmol) and 1-(6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl)ethanamine hydrochloride (164 mg, 0.57 mmol, Amine-6, single enantiomer), and sodium bicarbonate (240 mg, 2.3 mmol) as a base in a similar manner to Step-2 of Intermediate-1.

Sources & evidence

ORD record
ord-6d31444d1b1041ff964dc4833960af75
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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